NP-MRD: Showing NP-Card for Quinofuracin B (NP0013752)

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Record Information

Version

2.0

Created at

2021-01-05 23:01:20 UTC

Updated at

2021-07-15 17:15:21 UTC

NP-MRD ID

NP0013752

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Quinofuracin B

Provided By

NPAtlas

Description

Quinofuracin B is found in Staphylotrichum and Staphylotrichum boninense. Based on a literature review very few articles have been published on (2R,3R,4S,5S)-5-[(1R)-1,2-dihydroxyethyl]-4-hydroxy-2-{[(1S)-1-(1,3,6,8-tetrahydroxy-9,10-dioxo-9,10-dihydroanthracen-2-yl)hexyl]oxy}oxolan-3-yl acetate.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242119493D          

 73 76  0  0  0  0            999 V2000
   -0.0055    6.2769   -0.1085 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3848    5.1574    0.8107 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.8332    3.8927    0.0849 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2605    3.3949   -0.8229 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0910    2.1195   -1.5648 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3320    0.9654   -0.6730 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.3786    1.0569    0.2042 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4865    0.3423   -0.2422 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.6287    1.0774   -0.2819 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7045    0.2431   -0.0633 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.6870    0.4196   -1.2132 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.0974    1.7466   -1.1996 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8579   -0.4981   -1.1396 C   0  0  1  0  0  0  0  0  0  0  0  0
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    1.9585   -0.0548   -0.7543 C   0  0  0  0  0  0  0  0  0  0  0  0
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    4.2071   -1.1656   -0.8991 C   0  0  0  0  0  0  0  0  0  0  0  0
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    5.2966   -1.9063   -0.3072 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4139   -2.2743   -1.0317 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5768   -1.9593   -2.3527 O   0  0  0  0  0  0  0  0  0  0  0  0
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    4.0008   -1.8798    1.8221 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8488   -2.1678    3.0401 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.2223    5.5256    1.4693 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.1447   -1.6544   -0.9580 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.8378   -0.8010    1.6055 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0601   -4.9351    0.7223 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1913   -3.9081   -0.4641 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.0897    0.6540    2.2293 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7455   -1.0550    2.9385 H   0  0  0  0  0  0  0  0  0  0  0  0
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    6.0176   -1.4821   -2.9666 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2880   -3.2923   -0.9262 H   0  0  0  0  0  0  0  0  0  0  0  0
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  1  2  1  0  0  0  0
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 34 70  1  0  0  0  0
 35 71  1  0  0  0  0
 37 72  1  0  0  0  0
 38 73  1  0  0  0  0
M  END

     RDKit          3D

 73 76  0  0  0  0  0  0  0  0999 V2000
   -0.0055    6.2769   -0.1085 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3848    5.1574    0.8107 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8332    3.8927    0.0849 C   0  0  0  0  0  0  0  0  0  0  0  0
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  1 43  1  0
  1 44  1  0
  2 45  1  0
  2 46  1  0
  3 47  1  0
  3 48  1  0
  4 49  1  0
  4 50  1  0
  5 51  1  0
  5 52  1  0
  6 53  1  6
  8 54  1  6
 10 55  1  1
 11 56  1  6
 12 57  1  0
 13 58  1  0
 13 59  1  0
 14 60  1  0
 15 61  1  6
 16 62  1  0
 17 63  1  1
 20 64  1  0
 20 65  1  0
 20 66  1  0
 24 67  1  0
 25 68  1  0
 29 69  1  0
 34 70  1  0
 35 71  1  0
 37 72  1  0
 38 73  1  0
M  END


  Mrv1652306242119493D          

 73 76  0  0  0  0            999 V2000
   -0.0055    6.2769   -0.1085 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3848    5.1574    0.8107 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.8332    3.8927    0.0849 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2605    3.3949   -0.8229 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0910    2.1195   -1.5648 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3320    0.9654   -0.6730 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.3786    1.0569    0.2042 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4865    0.3423   -0.2422 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.6287    1.0774   -0.2819 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7045    0.2431   -0.0633 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.6870    0.4196   -1.2132 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.0974    1.7466   -1.1996 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8579   -0.4981   -1.1396 C   0  0  1  0  0  0  0  0  0  0  0  0
   -7.6395   -0.3244    0.0028 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2261   -1.1765    0.0389 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.8922   -1.9311    0.9641 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7717   -0.9286    0.5226 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.9624   -2.0006    0.0903 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3573   -2.8449    0.9837 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5005   -3.9828    0.6017 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5364   -2.6489    2.2395 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8362    0.3089   -0.0487 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7488   -0.0554    1.3008 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2760    0.2314    2.1371 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8040   -0.7665    1.8637 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9058   -1.1143    1.1584 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0231   -0.7796   -0.1516 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9585   -0.0548   -0.7543 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1835    0.2093   -2.0728 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2071   -1.1656   -0.8991 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2179   -0.8028   -2.1167 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2966   -1.9063   -0.3072 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4139   -2.2743   -1.0317 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5768   -1.9593   -2.3527 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4230   -3.0019   -0.3833 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2854   -3.3290    0.9362 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2857   -4.0444    1.5588 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1701   -2.9565    1.6503 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1769   -2.2550    1.0511 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0008   -1.8798    1.8221 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8488   -2.1678    3.0401 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4727    6.1191   -1.1154 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3257    7.2744    0.2565 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1093    6.2831   -0.2909 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2223    5.5256    1.4693 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4153    4.8803    1.5188 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.0901    3.1799    0.8804 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1868    3.2804   -0.2322 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4943    4.1974   -1.5691 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4839    2.0102   -2.4484 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1660    2.3529   -1.9860 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6928    0.1612   -1.4756 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2585   -0.0299   -1.2911 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1786    0.5517    0.8993 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1219    0.2160   -2.1472 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0858    2.0530   -0.2454 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5210   -0.2881   -2.0120 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5154   -1.5290   -1.2098 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1624    0.0887    0.7576 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1447   -1.6544   -0.9580 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2202   -2.7502    0.5104 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8378   -0.8010    1.6055 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0601   -4.9351    0.7223 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1913   -3.9081   -0.4641 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4144   -4.0880    1.2543 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0897    0.6540    2.2293 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7455   -1.0550    2.9385 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7454    0.5830   -2.7839 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0176   -1.4821   -2.9666 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2880   -3.2923   -0.9262 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1962   -5.0715    1.5199 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0546   -3.2160    2.7053 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
 10 15  1  0  0  0  0
 15 16  1  0  0  0  0
 15 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 19 21  2  0  0  0  0
  6 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 23 25  1  0  0  0  0
 25 26  2  0  0  0  0
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 27 28  2  0  0  0  0
 28 29  1  0  0  0  0
 27 30  1  0  0  0  0
 30 31  2  0  0  0  0
 30 32  1  0  0  0  0
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 33 34  1  0  0  0  0
 33 35  1  0  0  0  0
 35 36  2  0  0  0  0
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 36 38  1  0  0  0  0
 38 39  2  0  0  0  0
 39 40  1  0  0  0  0
 40 41  2  0  0  0  0
 17  8  1  0  0  0  0
 28 22  1  0  0  0  0
 39 32  1  0  0  0  0
 40 26  1  0  0  0  0
  1 42  1  0  0  0  0
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  6 53  1  6  0  0  0
  8 54  1  6  0  0  0
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 29 69  1  0  0  0  0
 34 70  1  0  0  0  0
 35 71  1  0  0  0  0
 37 72  1  0  0  0  0
 38 73  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0013752

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC1=C([H])C(O[H])=C2C(=O)C3=C(O[H])C(=C(O[H])C([H])=C3C(=O)C2=C1[H])[C@@]([H])(O[C@]1([H])O[C@@]([H])([C@]([H])(O[H])C([H])([H])O[H])[C@]([H])(O[H])[C@@]1([H])OC(=O)C([H])([H])[H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C28H32O13/c1-3-4-5-6-18(40-28-27(39-11(2)30)25(38)26(41-28)17(34)10-29)21-16(33)9-14-20(24(21)37)23(36)19-13(22(14)35)7-12(31)8-15(19)32/h7-9,17-18,25-29,31-34,37-38H,3-6,10H2,1-2H3/t17-,18+,25+,26+,27-,28-/m1/s1

> <INCHI_KEY>
RUWRWSMREJGOBH-YIENMFSPSA-N

> <FORMULA>
C28H32O13

> <MOLECULAR_WEIGHT>
576.551

> <EXACT_MASS>
576.18429109

> <JCHEM_ACCEPTOR_COUNT>
12

> <JCHEM_ATOM_COUNT>
73

> <JCHEM_AVERAGE_POLARIZABILITY>
57.886747213305775

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
7

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2R,3R,4S,5S)-5-[(1R)-1,2-dihydroxyethyl]-4-hydroxy-2-{[(1S)-1-(1,3,6,8-tetrahydroxy-9,10-dioxo-9,10-dihydroanthracen-2-yl)hexyl]oxy}oxolan-3-yl acetate

> <ALOGPS_LOGP>
2.14

> <JCHEM_LOGP>
3.180188199999999

> <ALOGPS_LOGS>
-2.66

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
7.457935981458421

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.772696660004103

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9745072612323424

> <JCHEM_POLAR_SURFACE_AREA>
220.51

> <JCHEM_REFRACTIVITY>
140.20109999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
11

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.25e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2R,3R,4S,5S)-5-[(1R)-1,2-dihydroxyethyl]-4-hydroxy-2-{[(1S)-1-(1,3,6,8-tetrahydroxy-9,10-dioxoanthracen-2-yl)hexyl]oxy}oxolan-3-yl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 73 76  0  0  0  0  0  0  0  0999 V2000
   -0.0055    6.2769   -0.1085 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3848    5.1574    0.8107 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8332    3.8927    0.0849 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2605    3.3949   -0.8229 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0910    2.1195   -1.5648 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3320    0.9654   -0.6730 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.3786    1.0569    0.2042 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4865    0.3423   -0.2422 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.6287    1.0774   -0.2819 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7045    0.2431   -0.0633 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.6870    0.4196   -1.2132 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.0974    1.7466   -1.1996 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8579   -0.4981   -1.1396 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6395   -0.3244    0.0028 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.8922   -1.9311    0.9641 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7717   -0.9286    0.5226 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.9624   -2.0006    0.0903 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.5364   -2.6489    2.2395 O   0  0  0  0  0  0  0  0  0  0  0  0
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    0.7488   -0.0554    1.3008 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2760    0.2314    2.1371 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8040   -0.7665    1.8637 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9058   -1.1143    1.1584 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0231   -0.7796   -0.1516 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.1835    0.2093   -2.0728 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2071   -1.1656   -0.8991 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2179   -0.8028   -2.1167 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2966   -1.9063   -0.3072 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4139   -2.2743   -1.0317 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5768   -1.9593   -2.3527 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4230   -3.0019   -0.3833 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2854   -3.3290    0.9362 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2857   -4.0444    1.5588 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1701   -2.9565    1.6503 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1769   -2.2550    1.0511 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0008   -1.8798    1.8221 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8488   -2.1678    3.0401 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4727    6.1191   -1.1154 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3257    7.2744    0.2565 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1093    6.2831   -0.2909 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2223    5.5256    1.4693 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.7686    4.0969   -0.4831 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.6928    0.1612   -1.4756 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2585   -0.0299   -1.2911 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -7.5210   -0.2881   -2.0120 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5154   -1.5290   -1.2098 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1624    0.0887    0.7576 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1447   -1.6544   -0.9580 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2202   -2.7502    0.5104 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8378   -0.8010    1.6055 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.1913   -3.9081   -0.4641 H   0  0  0  0  0  0  0  0  0  0  0  0
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    6.0546   -3.2160    2.7053 H   0  0  0  0  0  0  0  0  0  0  0  0
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 19 21  2  0
  6 22  1  0
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 17  8  1  0
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 38 73  1  0
M  END

HEADER    PROTEIN                                 24-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-JUN-21         0                                  
HETATM    1  C   UNK     0      -0.006   6.277  -0.109  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.385   5.157   0.811  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.833   3.893   0.085  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.261   3.395  -0.823  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.091   2.119  -1.565  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.332   0.965  -0.673  0.00  0.00           C+0
HETATM    7  O   UNK     0      -1.379   1.057   0.204  0.00  0.00           O+0
HETATM    8  C   UNK     0      -2.486   0.342  -0.242  0.00  0.00           C+0
HETATM    9  O   UNK     0      -3.629   1.077  -0.282  0.00  0.00           O+0
HETATM   10  C   UNK     0      -4.705   0.243  -0.063  0.00  0.00           C+0
HETATM   11  C   UNK     0      -5.687   0.420  -1.213  0.00  0.00           C+0
HETATM   12  O   UNK     0      -6.097   1.747  -1.200  0.00  0.00           O+0
HETATM   13  C   UNK     0      -6.858  -0.498  -1.140  0.00  0.00           C+0
HETATM   14  O   UNK     0      -7.640  -0.324   0.003  0.00  0.00           O+0
HETATM   15  C   UNK     0      -4.226  -1.177   0.039  0.00  0.00           C+0
HETATM   16  O   UNK     0      -4.892  -1.931   0.964  0.00  0.00           O+0
HETATM   17  C   UNK     0      -2.772  -0.929   0.523  0.00  0.00           C+0
HETATM   18  O   UNK     0      -1.962  -2.001   0.090  0.00  0.00           O+0
HETATM   19  C   UNK     0      -1.357  -2.845   0.984  0.00  0.00           C+0
HETATM   20  C   UNK     0      -0.500  -3.983   0.602  0.00  0.00           C+0
HETATM   21  O   UNK     0      -1.536  -2.649   2.240  0.00  0.00           O+0
HETATM   22  C   UNK     0       0.836   0.309  -0.049  0.00  0.00           C+0
HETATM   23  C   UNK     0       0.749  -0.055   1.301  0.00  0.00           C+0
HETATM   24  O   UNK     0      -0.276   0.231   2.137  0.00  0.00           O+0
HETATM   25  C   UNK     0       1.804  -0.767   1.864  0.00  0.00           C+0
HETATM   26  C   UNK     0       2.906  -1.114   1.158  0.00  0.00           C+0
HETATM   27  C   UNK     0       3.023  -0.780  -0.152  0.00  0.00           C+0
HETATM   28  C   UNK     0       1.958  -0.055  -0.754  0.00  0.00           C+0
HETATM   29  O   UNK     0       2.184   0.209  -2.073  0.00  0.00           O+0
HETATM   30  C   UNK     0       4.207  -1.166  -0.899  0.00  0.00           C+0
HETATM   31  O   UNK     0       4.218  -0.803  -2.117  0.00  0.00           O+0
HETATM   32  C   UNK     0       5.297  -1.906  -0.307  0.00  0.00           C+0
HETATM   33  C   UNK     0       6.414  -2.274  -1.032  0.00  0.00           C+0
HETATM   34  O   UNK     0       6.577  -1.959  -2.353  0.00  0.00           O+0
HETATM   35  C   UNK     0       7.423  -3.002  -0.383  0.00  0.00           C+0
HETATM   36  C   UNK     0       7.285  -3.329   0.936  0.00  0.00           C+0
HETATM   37  O   UNK     0       8.286  -4.044   1.559  0.00  0.00           O+0
HETATM   38  C   UNK     0       6.170  -2.957   1.650  0.00  0.00           C+0
HETATM   39  C   UNK     0       5.177  -2.255   1.051  0.00  0.00           C+0
HETATM   40  C   UNK     0       4.001  -1.880   1.822  0.00  0.00           C+0
HETATM   41  O   UNK     0       3.849  -2.168   3.040  0.00  0.00           O+0
HETATM   42  H   UNK     0      -0.473   6.119  -1.115  0.00  0.00           H+0
HETATM   43  H   UNK     0      -0.326   7.274   0.257  0.00  0.00           H+0
HETATM   44  H   UNK     0       1.109   6.283  -0.291  0.00  0.00           H+0
HETATM   45  H   UNK     0      -1.222   5.526   1.469  0.00  0.00           H+0
HETATM   46  H   UNK     0       0.415   4.880   1.519  0.00  0.00           H+0
HETATM   47  H   UNK     0      -1.769   4.097  -0.483  0.00  0.00           H+0
HETATM   48  H   UNK     0      -1.090   3.180   0.880  0.00  0.00           H+0
HETATM   49  H   UNK     0       1.187   3.280  -0.232  0.00  0.00           H+0
HETATM   50  H   UNK     0       0.494   4.197  -1.569  0.00  0.00           H+0
HETATM   51  H   UNK     0       0.484   2.010  -2.448  0.00  0.00           H+0
HETATM   52  H   UNK     0      -1.166   2.353  -1.986  0.00  0.00           H+0
HETATM   53  H   UNK     0      -0.693   0.161  -1.476  0.00  0.00           H+0
HETATM   54  H   UNK     0      -2.259  -0.030  -1.291  0.00  0.00           H+0
HETATM   55  H   UNK     0      -5.179   0.552   0.899  0.00  0.00           H+0
HETATM   56  H   UNK     0      -5.122   0.216  -2.147  0.00  0.00           H+0
HETATM   57  H   UNK     0      -6.086   2.053  -0.245  0.00  0.00           H+0
HETATM   58  H   UNK     0      -7.521  -0.288  -2.012  0.00  0.00           H+0
HETATM   59  H   UNK     0      -6.515  -1.529  -1.210  0.00  0.00           H+0
HETATM   60  H   UNK     0      -7.162   0.089   0.758  0.00  0.00           H+0
HETATM   61  H   UNK     0      -4.145  -1.654  -0.958  0.00  0.00           H+0
HETATM   62  H   UNK     0      -5.220  -2.750   0.510  0.00  0.00           H+0
HETATM   63  H   UNK     0      -2.838  -0.801   1.605  0.00  0.00           H+0
HETATM   64  H   UNK     0      -1.060  -4.935   0.722  0.00  0.00           H+0
HETATM   65  H   UNK     0      -0.191  -3.908  -0.464  0.00  0.00           H+0
HETATM   66  H   UNK     0       0.414  -4.088   1.254  0.00  0.00           H+0
HETATM   67  H   UNK     0      -1.090   0.654   2.229  0.00  0.00           H+0
HETATM   68  H   UNK     0       1.746  -1.055   2.938  0.00  0.00           H+0
HETATM   69  H   UNK     0       1.745   0.583  -2.784  0.00  0.00           H+0
HETATM   70  H   UNK     0       6.018  -1.482  -2.967  0.00  0.00           H+0
HETATM   71  H   UNK     0       8.288  -3.292  -0.926  0.00  0.00           H+0
HETATM   72  H   UNK     0       8.196  -5.072   1.520  0.00  0.00           H+0
HETATM   73  H   UNK     0       6.055  -3.216   2.705  0.00  0.00           H+0
CONECT    1    2   42   43   44                                             
CONECT    2    1    3   45   46                                             
CONECT    3    2    4   47   48                                             
CONECT    4    3    5   49   50                                             
CONECT    5    4    6   51   52                                             
CONECT    6    5    7   22   53                                             
CONECT    7    6    8                                                       
CONECT    8    7    9   17   54                                             
CONECT    9    8   10                                                       
CONECT   10    9   11   15   55                                             
CONECT   11   10   12   13   56                                             
CONECT   12   11   57                                                       
CONECT   13   11   14   58   59                                             
CONECT   14   13   60                                                       
CONECT   15   10   16   17   61                                             
CONECT   16   15   62                                                       
CONECT   17   15   18    8   63                                             
CONECT   18   17   19                                                       
CONECT   19   18   20   21                                                  
CONECT   20   19   64   65   66                                             
CONECT   21   19                                                            
CONECT   22    6   23   28                                                  
CONECT   23   22   24   25                                                  
CONECT   24   23   67                                                       
CONECT   25   23   26   68                                                  
CONECT   26   25   27   40                                                  
CONECT   27   26   28   30                                                  
CONECT   28   27   29   22                                                  
CONECT   29   28   69                                                       
CONECT   30   27   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30   33   39                                                  
CONECT   33   32   34   35                                                  
CONECT   34   33   70                                                       
CONECT   35   33   36   71                                                  
CONECT   36   35   37   38                                                  
CONECT   37   36   72                                                       
CONECT   38   36   39   73                                                  
CONECT   39   38   40   32                                                  
CONECT   40   39   41   26                                                  
CONECT   41   40                                                            
CONECT   42    1                                                            
CONECT   43    1                                                            
CONECT   44    1                                                            
CONECT   45    2                                                            
CONECT   46    2                                                            
CONECT   47    3                                                            
CONECT   48    3                                                            
CONECT   49    4                                                            
CONECT   50    4                                                            
CONECT   51    5                                                            
CONECT   52    5                                                            
CONECT   53    6                                                            
CONECT   54    8                                                            
CONECT   55   10                                                            
CONECT   56   11                                                            
CONECT   57   12                                                            
CONECT   58   13                                                            
CONECT   59   13                                                            
CONECT   60   14                                                            
CONECT   61   15                                                            
CONECT   62   16                                                            
CONECT   63   17                                                            
CONECT   64   20                                                            
CONECT   65   20                                                            
CONECT   66   20                                                            
CONECT   67   24                                                            
CONECT   68   25                                                            
CONECT   69   29                                                            
CONECT   70   34                                                            
CONECT   71   35                                                            
CONECT   72   37                                                            
CONECT   73   38                                                            
MASTER        0    0    0    0    0    0    0    0   73    0  152    0
END

RDKit          3D

73 76  0  0  0  0  0  0  0  0999 V2000
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   -6.5154   -1.5290   -1.2098 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1624    0.0887    0.7576 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1447   -1.6544   -0.9580 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2202   -2.7502    0.5104 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8378   -0.8010    1.6055 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0601   -4.9351    0.7223 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1913   -3.9081   -0.4641 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4144   -4.0880    1.2543 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0897    0.6540    2.2293 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7455   -1.0550    2.9385 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7454    0.5830   -2.7839 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0176   -1.4821   -2.9666 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2880   -3.2923   -0.9262 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1962   -5.0715    1.5199 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0546   -3.2160    2.7053 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 11 13  1  0
 13 14  1  0
 10 15  1  0
 15 16  1  0
 15 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 19 21  2  0
  6 22  1  0
 22 23  2  0
 23 24  1  0
 23 25  1  0
 25 26  2  0
 26 27  1  0
 27 28  2  0
 28 29  1  0
 27 30  1  0
 30 31  2  0
 30 32  1  0
 32 33  2  0
 33 34  1  0
 33 35  1  0
 35 36  2  0
 36 37  1  0
 36 38  1  0
 38 39  2  0
 39 40  1  0
 40 41  2  0
 17  8  1  0
 28 22  1  0
 39 32  1  0
 40 26  1  0
  1 42  1  0
  1 43  1  0
  1 44  1  0
  2 45  1  0
  2 46  1  0
  3 47  1  0
  3 48  1  0
  4 49  1  0
  4 50  1  0
  5 51  1  0
  5 52  1  0
  6 53  1  6
  8 54  1  6
 10 55  1  1
 11 56  1  6
 12 57  1  0
 13 58  1  0
 13 59  1  0
 14 60  1  0
 15 61  1  6
 16 62  1  0
 17 63  1  1
 20 64  1  0
 20 65  1  0
 20 66  1  0
 24 67  1  0
 25 68  1  0
 29 69  1  0
 34 70  1  0
 35 71  1  0
 37 72  1  0
 38 73  1  0
M  END

View in JSmol View NMR Assignments

Synonyms

Value	Source
(2R,3R,4S,5S)-5-[(1R)-1,2-Dihydroxyethyl]-4-hydroxy-2-{[(1S)-1-(1,3,6,8-tetrahydroxy-9,10-dioxo-9,10-dihydroanthracen-2-yl)hexyl]oxy}oxolan-3-yl acetic acid	Generator

Chemical Formula

C₂₈H₃₂O₁₃

Average Mass

576.5510 Da

Monoisotopic Mass

576.18429 Da

IUPAC Name

(2R,3R,4S,5S)-5-[(1R)-1,2-dihydroxyethyl]-4-hydroxy-2-{[(1S)-1-(1,3,6,8-tetrahydroxy-9,10-dioxo-9,10-dihydroanthracen-2-yl)hexyl]oxy}oxolan-3-yl acetate

Traditional Name

(2R,3R,4S,5S)-5-[(1R)-1,2-dihydroxyethyl]-4-hydroxy-2-{[(1S)-1-(1,3,6,8-tetrahydroxy-9,10-dioxoanthracen-2-yl)hexyl]oxy}oxolan-3-yl acetate

CAS Registry Number

Not Available

SMILES

CCCCC[C@H](O[C@@H]1O[C@@H]([C@H](O)CO)[C@H](O)[C@H]1OC(C)=O)C1=C(O)C=C2C(=O)C3=CC(O)=CC(O)=C3C(=O)C2=C1O

InChI Identifier

InChI=1S/C28H32O13/c1-3-4-5-6-18(40-28-27(39-11(2)30)25(38)26(41-28)17(34)10-29)21-16(33)9-14-20(24(21)37)23(36)19-13(22(14)35)7-12(31)8-15(19)32/h7-9,17-18,25-29,31-34,37-38H,3-6,10H2,1-2H3/t17-,18+,25+,26+,27-,28-/m1/s1

InChI Key

RUWRWSMREJGOBH-YIENMFSPSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Staphylotrichum	NPAtlas	25611347
Staphylotrichum boninense	LOTUS Database	35616633

Chemical Taxonomy

Classification

Not classified

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	2.14	ALOGPS
logP	3.18	ChemAxon
logS	-2.7	ALOGPS
pKa (Strongest Acidic)	6.77	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	12	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	220.51 Å²	ChemAxon
Rotatable Bond Count	11	ChemAxon
Refractivity	140.2 m³·mol⁻¹	ChemAxon
Polarizability	57.89 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

NPAtlas ID

NPA004114

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

58986514

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

118735492

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for Quinofuracin B (NP0013752)

MOL for NP0013752 (Quinofuracin B)

3D MOL for NP0013752 (Quinofuracin B)

3D SDF for NP0013752 (Quinofuracin B)

3D-SDF for NP0013752 (Quinofuracin B)

PDB for NP0013752 (Quinofuracin B)

3D PDB for NP0013752 (Quinofuracin B)

SMILES for NP0013752 (Quinofuracin B)

INCHI for NP0013752 (Quinofuracin B)

Structure for NP0013752 (Quinofuracin B)

3D Structure for NP0013752 (Quinofuracin B)